Triphenylphosphine → HCID 66877137, compound

7.128 mmol of triphenylphosphine are added to a solution of 5.940 mmol of (3S,4R,5R)-3-azidomethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester in 20 ml of methanol, 20 ml of tetrahydrofuran, 5 ml of water and 3.56 ml of concentrated aqueous ammonia (25%) at room temperature. After overnight stirring, the reaction mixture is partitioned between tert-butyl methyl ether and 5:1 water/saturated aqueous sodium bicarbonate solution. The aqueous layer is extracted with tert-butyl methyl ether—the combined organic layers are washed successively with water and brine, dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound as a yellow oil. Rf=0.42 (dichloromethane-methanol-25% ammonia conc. 200:20:1); Rt=4.64 (gradient I).

1. customthe reaction mixture is partitioned between tert-butyl methyl ether and 5:1 water/saturated aqueous sodium bicarbonate solution
2. extractionThe aqueous layer is extracted with tert-butyl methyl ether—the combined organic layers
3. washare washed successively with water and brine
4. dry with materialdried with sodium sulfate
5. customevaporated
6. customThe residue is purified by flash chromatography (SiO2 60F)

ORD record

ord-949a414a1d9549018559b49ecdf62e7a

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625893B2